Journal of the American Oil Chemists’ Society

, Volume 76, Issue 10, pp 1139–1142

Enzymatic synthesis of l-menthyl esters in organic solvent-free system

  • Yuji Shimada
  • Yoshinori Hirota
  • Takashi Baba
  • Shinichiro Kato
  • Akio Sugihara
  • Shigeru Moriyama
  • Yoshio Tominaga
  • Tadamasa Terai
Article

DOI: 10.1007/s11746-999-0086-3

Cite this article as:
Shimada, Y., Hirota, Y., Baba, T. et al. J Am Oil Chem Soc (1999) 76: 1139. doi:10.1007/s11746-999-0086-3

Abstract

l-Menthol has been widely used as a food additive and an ingredient of cosmetics, and it is esterified to moderate the strong flavor. We attempted esterification of l-menthol with long-chain unsaturated fatty acid in an organic solvent-free enzymatic system. Commercially available lipases were screened, and Candida rugosa lipase was selected as a catalyst. Several factors affecting the esterification were investigated, and the reaction conditions were determined as follows: A reaction mixture of l-menthol/fatty acid (1:3, mol/mol), 30% water, and 700 units of the lipase per gram of reaction mixture was incubated at 30°C with stirring. After 24 h under these conditions, the esterification extents of l-menthol with oleic, linoleic, and α-linolenic acids reached 96, 88, and 95%, respectively. The structure of the esterified product was confirmed by mass, infrared, and nuclear magnetic resonance spectroscopies. Bacause Candida lipase acted strongly on l-menthol and very weakly on d-menthol, dl-menthol was esterified with oleic acid under the same conditions. The reaction showed high enantioselectivity; the enantiomeric ratio (E) was 31, and enantiomeric excess (ee) of l-menthyl oleate reached 88% after 32 h.

Key words

Candida rugosa esterification fatty acids lipase menthol optical resolution 

Copyright information

© AOCS Press 1999

Authors and Affiliations

  • Yuji Shimada
    • 3
  • Yoshinori Hirota
    • 1
  • Takashi Baba
    • 2
  • Shinichiro Kato
    • 1
  • Akio Sugihara
    • 3
  • Shigeru Moriyama
    • 2
  • Yoshio Tominaga
    • 3
  • Tadamasa Terai
    • 1
  1. 1.Department of Applied ChemistryOsaka Institute of TechnologyOsakaJapan
  2. 2.Maruha Corp.IbarakiJapan
  3. 3.Municipal Technical Research InstituteOsakaJapan